Selective acylations of multifunctional nucleophiles, including carbohydrates and nucleosides, with intermediates generated by Wolff rearrangement of amino acid derived diazo ketones: Preparation of beta-amino acid derivatives

被引:35
作者
Guibourdenche, C
Podlech, J
Seebach, D
机构
[1] Laboratorium für Organische Chemie, Eidgenössischen Technischen Hochschule, ETH-Zentrum, CH 8092 Zürich
[2] Universität Stuttgart, Institut für Organische Chemie und Isotopenforschung, D-70569 Stuttgart
来源
LIEBIGS ANNALEN | 1996年 / 07期
关键词
Arndt-Eistert homologation of amino acids; Wolff rearrangement; beta-amino acid esters of xylose and sucrose; 5'-nucleoside esters of (3'S)-3-aminocarboxylic acids; thymidine; adenosine; deoxyadenosine;
D O I
10.1002/jlac.199619960710
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The diazo ketones derived from Z- and Boc-protected alanine, valine, and alanyl-alanine (1-5) were decomposed by catalytic amounts of silver benzoate/Et(3)N in the presence of polyfunctional nucleophiles such as 3-methyl-1,3-butanediol, 2-aminoethanol, carbohydrates (xylofuranose and sucrose) and nucleosides (thymidine, adenosine derivatives). In many cases, products of beta-amino acylations are formed (6-14, 15b, 17-19, 21, 23, 24) with surprising functional group selectivities. The scope and limitations of the method are described.
引用
收藏
页码:1121 / 1129
页数:9
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